p-Toluenesulfonic acid → HCID 357800, compound

HRID 1834341Notes

Reaction equation

HRID 1834341 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 357781Ethyl 6-hydroxyhexanoate

Product 1

HCID 357800HCID 357800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 66 g. of ethyl 6-hydroxyhexanoate in 400 ml. of methylene chloride were added 1 g. of p-toluenesulphonic acid and 45 g. of 2,3-dihydropyran and the mixture was stirred at 25° C. for 20 minutes. The reaction mixture was then washed with an aqueous solution of sodium bicarbonate, dried and concentrated. The residue was distilled in vacuo to obtain 77 g. of the title compound having the following physical characteristics:-

Workup

  1. washThe reaction mixture was then washed with an aqueous solution of sodium bicarbonate
  2. customdried
  3. concentrationconcentrated
  4. distillationThe residue was distilled in vacuo
  5. customto obtain 77 g

Sources & evidence

ORD record
ord-0e94f2800c3e45c7a7a471ff4afc99c6
Source dataset
uspto-grants-1978_01
Patent number
US04069387

Reaction notes

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